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Crown ether catalyzed deuterium exchange in the synthesis of benzyl cyanides
Author(s) -
Davis Bruce
Publication year - 1987
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580240209
Subject(s) - chemistry , ethylamine , cyanide , medicinal chemistry , catalysis , nucleophilic substitution , solvent , ether , crown ether , benzyl alcohol , organic chemistry , cyclohexane , nucleophile , ion
Nucleophilic substitution of benzyl‐type chlorides with cyanide ion in deuterochloroform, deuteroacetonitrile or deuterobenzene catalyzed by 18‐crown‐6 results in the introduction of deuterium onto the benzyl carbon. Benzyl cyanides are labelled by refluxing with cyanide ion and crown ether in deutero solvent. Two such exchanges in deuterochloroform produced greater than 90% incorporation. Side‐chain labelled phenyl‐ethylamine, tryptamine and m ‐ and p ‐tyramine were synthesized in this way.